Page last updated: 2024-11-10

2-(3-trifluoromethylphenyl)histamine

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Description

2-(3-trifluoromethylphenyl)histamine: a selective histamine H1-receptor agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5310982
CHEMBL ID24665
SCHEMBL ID3012997
MeSH IDM0244680

Synonyms (10)

Synonym
2-[3-(trifluoromethyl)phenyl]histamine
NCGC00165906-01
CHEMBL24665 ,
L000054
2-[2-[3-(trifluoromethyl)phenyl]-1h-imidazol-5-yl]ethanamine
2-(3-trifluoromethylphenyl)histamine
bdbm50403672
SCHEMBL3012997
2-(3-(trifluormethyl)phenyl)-histamine
nfuyvkmagijykb-uhfffaoysa-n
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H1 receptorRattus norvegicus (Norway rat)IC50 (µMol)1.00000.00000.32271.2589AID87362
Histamine H1 receptorRattus norvegicus (Norway rat)Ki251,189,002,240.00000.00071.54406.5000AID87372
Histamine H1 receptorHomo sapiens (human)IC50 (µMol)1.00000.00000.44365.1768AID87362
Histamine H1 receptorHomo sapiens (human)Ki251,189,002,240.00000.00000.511010.0000AID87372
Histamine H4 receptorHomo sapiens (human)Ki1.25890.00060.478710.0000AID548981
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H1 receptorCavia porcellus (domestic guinea pig)Kd0.00100.00080.12280.9550AID86904
Histamine H1 receptorHomo sapiens (human)EC50 (µMol)0.25120.00040.18810.7943AID548979
Histamine H4 receptorHomo sapiens (human)EC50 (µMol)1.58490.00740.601610.0000AID548982
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
inflammatory responseHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
memoryHistamine H1 receptorHomo sapiens (human)
visual learningHistamine H1 receptorHomo sapiens (human)
regulation of vascular permeabilityHistamine H1 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H1 receptorHomo sapiens (human)
regulation of synaptic plasticityHistamine H1 receptorHomo sapiens (human)
cellular response to histamineHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H1 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H1 receptorHomo sapiens (human)
inflammatory responseHistamine H4 receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationHistamine H4 receptorHomo sapiens (human)
biological_processHistamine H4 receptorHomo sapiens (human)
regulation of MAPK cascadeHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H4 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H4 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H4 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
histamine receptor activityHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H1 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H1 receptorHomo sapiens (human)
histamine receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H4 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H4 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
cytosolHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
synapseHistamine H1 receptorHomo sapiens (human)
dendriteHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
plasma membraneHistamine H4 receptorHomo sapiens (human)
dendriteHistamine H4 receptorHomo sapiens (human)
synapseHistamine H4 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID86901Contractile effects antagonized by mepyramine (0.3-100 nM) against Histamine H1 receptor in guinea pig ileum1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID87056Contractile effects on guinea pig aorta as histamine H1 receptor agonism1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID548982Agonist activity at human recombinant histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma2 by steady-state GTPase activity assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID87372Inhibitory activity against human Histamine H1 receptor2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
AID86276In vivo binding of H1 receptor Agonists measured by binding of [3H]mepyramine to Mouse cerebral cortex at the dosage of ( 100 mg/kg(no. of mice treated= 3 )1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID86904Compound was tested for the contractile effects antagonized by mepyramine (1-1000 nM) against Histamine H1 receptor of guinea pig aorta.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86603H1-Histamine receptor agonism on guinea pig ileum as intrinsic activity given as 1.0 with respect to histamine (paired 't'test; p>0.05).1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID86406In vivo binding of H1 receptor Agonists measured by binding of [3H]mepyramine to Mouse cerebral cortex at the dosage of ( 30 mg/kg(no. of mice treated= 5 )1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID87058The H1 receptor-mediated nature of the ileum contractionhas been verified by competition experiments with the H1 receptor antagonist mepyramine1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID101737Compound was tested for its agonist activity against M3-acetylcholine receptor of guinea pig ileum.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86750Contractile effect on isolated guinea pig ileal segments is a measure of H1 (histamine) receptor agonistic activity relative to histamine.1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID88160Histamine H2 receptor agonism activity was determined on the isolated Guinea pig Atrium was determined as pD'21995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID86749Contractile effect on isolated guinea pig aorta is a measure of H1 (histamine) receptor agonistic activity relative to histamine1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID88002Histamine H2 receptor agonism activity was determined on the isolated Guinea pig Atrium was determined as Intrinsic activity with respect to Histamine1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID86926H1-Histamine receptor agonism on Guinea pig aorta was evaluated (SEM 0.03-0.18)1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID548990Selectivity ratio of EC50 for human histamine H1 receptor to EC50 for human histamine H4 receptor2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID86407In vivo binding of H1 receptor Agonists measured by binding of [3H]-Mepyramine to Mouse cerebral cortex at the dosage of ( 300 mg/kg(no. of mice treated= 3 )1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID86405In vivo binding of H1 receptor Agonists measured by binding of [3H]mepyramine to Mouse cerebral cortex at the dosage of ( 3 mg/kg(no. of mice treated=5 )1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID88167Compound was tested for agonist activity against histamine H2 receptor of guinea pig atrium1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86416Compound was tested for its partial agonist activity in the presence of 1 nM mepyramine against Histamine H1 receptor in guinea pig ileum.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86418Compound was tested for its partial agonist activity in the presence of 10 nM mepyramine against Histamine H1 receptor in guinea pig ileum.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID87070Compound was tested for binding affinity against guinea pig ileum1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID548983Agonist activity at human recombinant histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma2 by steady-state GTPase activity assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID87227Intrinsic activity was determined2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
AID86419Compound was tested for its partial agonist activity in the presence of 100 nM mepyramine against Histamine H1 receptor in guinea pig ileum.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86917Contractile effect on isolated guinea pig ileal segments by H1 (histamine) receptor agonism.1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID548979Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID548980Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay relative to histamine2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID86598H1-Histamine receptor agonism on Guinea pig aorta was evaluated as Intrinsic activity given as 1.0 with respect to histamine (paired 't'test;p>0.05)1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID87362Inhibitory activity against human Histamine H1 receptor2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists.
AID86424Partial agonist activity against Histamine H1 receptor in guinea pig aorta1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID548981Displacement of [3H]-histamine from human histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma22010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Histamine H4 receptor agonists.
AID86425Partial agonist activity against Histamine H1 receptor in guinea pig ileum.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86754Relative potency against Histamine H1 receptor of guinea pig aorta1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86753Relative potency against Histamine H1 receptor in guinea pig ileum.1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
AID86275In vivo binding of H1 receptor Agonists measured by binding of [3H]mepyramine to Mouse cerebral cortex at the dosage of ( 10 mg/kg(no. of mice treated=5 )1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Synthesis and histamine H1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues.
AID86288Compound was tested for the agonist activity against histamine H3 receptor of guinea pig ileum1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
N alpha-alkylated derivatives of 2-phenylhistamines: synthesis and in vitro activity of potent histamine H1-receptor agonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (41.67)18.2507
2000's4 (33.33)29.6817
2010's3 (25.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.74 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]